1613367-24-0Relevant academic research and scientific papers
Complementarity of 2,6-Dimethanolpyridine and Di(ethylene glycol) in the Complexation of Na+Ions: Attaching Multiple Copies of [2]Catenane Branches to Isophthalaldehyde-Containing Cores
Chen, Ching-Yu,Chiu, Sheng-Hsien,Ho, Tsung-Hsien,Hsu, Chun-Ju,Lai, Chien-Chen,Liu, Yi-Hung,Peng, Shie-Ming,Xu, Han-Chen
, p. 13491 - 13502 (2021/10/01)
In this study we found that 2,6-dimethanolpyridine displays good complementarity toward di(ethylene glycol) for the complexation of Na+ ions, allowing us to use this recognition system for the efficient synthesis of hetero[2]catenanes; indeed, it allowed us to attach multiple copies of [2]catenanes to branched systems presenting multiple isophthalaldehyde units. When we attempted to form a catenane from a preformed macrocycle featuring only a single di(ethylene glycol) unit, reacting it with a di(ethylene glycol) derivative presenting two amino termini, isophthalaldehyde, and templating Na+ ions [i.e., with the aim of using di(ethylene glycol)·Na+·di(ethylene glycol) recognition to template the formation of the interlocked imino macrocycle], the yields of the hetero[2]catenane and homo[2]catenane, comprising two imino macrocyclic units, were both poor (14% and 7%, respectively). In contrast, when one or two 2,6-dimethanolpyridine units were present in the preformed macrocycles, their reactions with the same diamine, dialdehyde, and Na+ ions provided the hetero[2]catenanes with high selectivity and efficiency (44% and 64% yields, respectively), with minimal formation of the competing homo[2]catenane. The high complementary of the 2,6-dimethanolpyridine·Na+·di(ethylene glycol) ligand pair allowed us to synthesize [2]catenane dimers and trimers directly from corresponding isophthalaldehyde-presenting cores, with yields, after subsequent reduction and methylation, of 42% and 31%, respectively.
CuAAC "click" active-template synthesis of functionalised [2]rotaxanes using small exo-substituted macrocycles: How small is too small?
Noor, Asif,Lo, Warrick K.C.,Moratti, Stephen C.,Crowley, James D.
supporting information, p. 7044 - 7047 (2014/06/23)
Two "small" 22- and 24-membered exo-alcohol functionalised pyridyl macrocycles are exploited in the CuAAC active-template synthesis of [2]rotaxanes. The 24-membered macrocycle forms [2]rotaxanes in good yields while the smaller 22-membered macrocycle does
